


Hey Handsome

by Piper_Halliwell1979



Category: Supernatural
Genre: Attraction, Castiel/Dean Winchester First Kiss, Castiel/Dean Winchester One Shot, Developing Relationship, Drinking & Talking, First Dates, First Kiss, First Time, Flirting, Fluff, Fluff and Smut, Frottage, Holding Hands, Hotel Sex, Jealousy, M/M, Non-Penetrative Sex, Pillow Talk, Possessive Castiel, Possessive Dean, Post-Coital Cuddling, Sam Is So Done, Supportive Sam, Third Wheel Sam
Language: English
Status: Completed
Published: 2017-12-02
Updated: 2017-12-02
Packaged: 2019-02-09 19:28:37
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,965
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12895101
Author URL: https://archiveofourown.org/users/Piper_Halliwell1979/pseuds/Piper_Halliwell1979
Summary: Castiel and the Winchesters go to a bar to unwind. Dean gets jealous of a waiter flirting with Cas. Sam calls him out and Cas admits something that kickstarts the relationship.





	Hey Handsome

Dean managed to find a bar that was kinda slow. They needed someplace they could unwind without thumping music and too many people. They grabbed a booth, Cas sliding in beside Dean, and Sam opposite them. A waiter came up to get their drink order.

 

“Scotch, neat, and whatever’s on tap,” Sam started.

 

“Same,” Dean agreed.

 

“And you, handsome?” The waiter smiled at Castiel. He shifted uncomfortably next to Dean at the flirtation.

 

“Three tequilas and a beer.”

 

Dean playfully nudged Cas’ shoulder. He straightened his back and looked around. No women, not even the staff. Whatever. Booze is booze. Sam took a queue from his brother and surveyed as well.

 

The waiter returned with their drinks and asked if they wanted any appetizers. Dean got them a plate of nachos. He ground his jaw a little when he caught the wink aimed at Cas.

 

Sam rolled his eyes. “I can’t believe you Dean.”

“What?” he said defensively.

 

“A waitress flirts with Cas and you call it a teachable moment. You practically get her number for him. A  _ waiter _ does the same thing and you almost growl at him. Did you ever stop to ask Cas if he’s into guys?” Sam looked over to Cas. He looked extremely uncomfortable being the topic of conversation.

 

“Okay. Cas, you into guys?” Dean asked him.

 

Cas quickly downed his shots in rapid succession. “I fail to see how gender correlates to attraction.”

 

Dean furrowed his brow. “Umm...that was about as clear as mud.”

 

“You, Dean, are aesthetically pleasing. Sam is as well. Attraction is deeper than appearance. There are many aspects to consider. I find you attractive but not your brother. No offense.”

 

Sam smirked. “None taken.” Now to see how Dean reacted to the revelation.

 

Before he could respond, the waiter returned with the nachos. He slipped them napkins and the one in front of Cas had a number on it. Dean switched it out for his own.

 

“Dude, I’m  _ right here _ . Can’t you see he’s with somebody?” It may have come out a little harsh so the waiter backed up with his hand and tray in a defensive position.

 

“Sorry. My mistake.”

 

“Dean?” Sam eyed him.

 

“What?”

 

“What the hell just happened?”

 

“Me and Cas are on a date now and you’re the annoying third wheel.” Dean dug into the food.

 

Cas beamed a little, smug grin on his face. His admission could have led to worse outcomes. “I’m your date?”

 

“Well, yeah. Asked you out for a drink, we’re sharing nachos.” He smiled wide for Cas. “You think I’m pretty,” he teased. It made Cas blush.

 

Sam shook his head. “Nine years of sexual tension and heart eyes and pining... _ this _ is what got you together?”

 

“Yeah. Now I know I got a shot. I  _ do _ have a shot, right?” Dean’s attention was back to Cas.

 

“I was always yours for the asking, Dean. You never expressed interest.” Cas picked at one of the chips, feigning eating if someone was watching.

 

Sam got out his phone and his wallet. After a minute Dean asked him what he was doing. “Getting my own room,” he answered. “Definity don’t want to be a third wheel for the whole date.”

 

“Are you implying Dean will expect intercourse after this?” Cas asked.

 

Both Winchesters choked on their beer. Dean wiped his mouth and chuckled nervously. “Easy there, tiger. It’s just a first date. Why don’t we try a few more of these before we take that step?”

 

“Oh.” Cas looked a little disappointed. “I would have been amenable to…”

 

“Check please!” Dean stood suddenly and threw some bills on the table. He handed Sam a twenty. “Cab money.” He pulled Cas up from the booth and led him outside by the hand. They weren’t even in the car yet when Dean put both hands on Cas’ face to kiss him. “Been wanting to do that for years."

 

Cas grabbed Dean’s jacket and kissed him back just as hard. “Me too.”

 

“We gonna make it back to the motel?” They exchanged a few more heated kisses up against his Baby.

 

“Would Sam bail us out for public indecency?” Cas countered. His hands were all over Dean.

 

“Good point. Get your ass in the car before we get arrested.” Dean fumbled to retrieve his keys from his pocket to unlock the door. Cas entered from the driver’s side and slid across. Dean leaned over for one last fevered kiss before willing himself to focus on driving.

 

Ten minutes felt closer to an hour. Dean was nervous and excited. Shit. What if he went of like thirty seconds into it? What the hell were they even gonna do? A little hand action? How would Cas feel if he asked for a blowjob? They’d have to take it as it came, so to speak.

 

Dean had Cas pinned up against the motel door. He was tongue deep and trying to get the door unlocked. Once the knob turned they were kicking off shoes and shedding outer layers, walking to the bed in the dark. Cas blindly searched the wall for a switch.

 

They fell to the closest bed with most of their clothes still on. Dean rutted on top of Cas. The moans gradually got louder and Cas had his hands down Dean’s back pockets to pull him even closer. “This...this is very arousing,” he said.

 

“So fucking hot, Cas. What do you wanna do about it?”

 

“I...I don’t know. You have so much more experience.”

 

“Not in this department. You wanna...ditch the pants?”

 

“Yes, please.”

 

Dean sat back on his knees so they could undo their belts. Neither took the time to fully shed their pants, just pushing them down to free their erections. Dean lowered himself back down on Cas and lined up their throbbing members. “Okay if I use my hand?”

 

“Yes. Touch me, Dean.”

 

He ran his palm over their heads to gather some precum. They were both on the thick side so his handspan barely encompassed them. Cas was already thrusting into his fist and Dean tried to match his rhythm. Their lips crashed together again and Dean was so close to shooting his wad.

 

“Dean...so close...feels so good.” Cas moaned. His blue eyes were nearly black from his lust blown pupils. He locked onto Dean for a few seconds then they rolled back in his head. His body tensed up and Dean felt the pulse on Cas’ shaft.

 

“Fuck!” He yelled when his own orgasm hit. He slowly milked them both before loosening his grip. He wiped the mess on the covers and fell breathless beside Cas. They panted then eventually evened out. “Wow, Cas. That was awesome!”

 

“That was very intense. And satisfying. I can only imagine how wonderful other means of sexual gratification will feel.”

 

“Well...there’s lots of stuff to try. I mean, if you’re up for it.”

 

“I’m undecided on penetration but I think oral sex might be fun.”

 

“Oh man, blowjobs are pretty sweet.”

 

“Dean?”

 

“Yeah?”

 

“Were you really just waiting for me to say something first?”

 

“I dunno. There’s been times I came close to saying something. I guess I convinced myself that you wouldn’t see me that way. Then I’d feel stupid and you’d be uncomfortable around me.”

 

Cas rolled to his side. “Don’t ever say you’re stupid. You’re highly intelligent and intuitive. You are also kind and loyal. You’re beautiful inside and out. I was the one convinced you could never see me as more. Had you and Sam not directly asked me…”

 

“I’m sorry we made you feel cornered, but I’m glad we got it out in the open. Speaking of,” Dean gestured to their current state of undress, “I’m gonna grab us a towel and we should probably put on something clean.”

 

Cas looked down at the drying semen on his shirt and stomach. “I’d forgotten that sex is messy.”

 

“We can always use rubbers,” Dean called from the bathroom. He emerged fully nude and holding a damp washcloth. Cas watched as he delicately cleaned him up. He got up to disrobe while Dean pulled some clothes from his duffle bag. “Here ya go. Sweatpants and a tee shirt. We’ll take some quarters and wash this stuff in the guest laundry tomorrow.”

 

Dean peeled back the soiled covers. Housekeeping aren’t strangers to bodily fluids. They still had the other queen sized bed to sleep in. They could just lay on the sheets of this one to watch a little TV.

 

Cas settled in beside Dean. Dean rested his head on Castiel’s shoulder and his hand on Cas’ thigh. Cas covered it with his own. “Are we in a relationship now?”

 

“I guess we are. You good with that?”

 

“Quite. How do you feel about it?”

 

“Scared. I’ve had exactly one long term relationship and it ended pretty bad. You were there. I don’t even say their names.”

 

“We’re  _ both _ hunters, Dean. We have seen each other’s darkness. We’ve lied to and hurt each other. And yet we’re still here and together. We’ve survived this long on faith in each other. Now is the time to have some faith in  _ us _ .”

 

“I do. Just...hear me out. I’m always going to be afraid of losing you. I  _ have _ lost you and it felt worse than getting hit by a truck. Which I have. Anyway, I’m gonna worry about you when you go off alone. I’m gonna get jealous and overprotective. I’m gonna be a real asshole sometimes because somebody flirts with you. I’m  _ that _ guy. So I’m scared that hanging onto you so tight is gonna push you away.”

 

“Oh, Dean. I’ve always known you were an asshole,” Cas said with a straight face. Dean gave him a Sam caliber bitchface until he cracked and laughed. Dean relaxed and shook his head.

 

“You’re funny. I’ll give you that.” Dean turned to snuggle into Cas’ arms. “Bottom line this for me. How do you see this going?”

 

Cas relished the warmth of Dean against him and the intimacy of just holding each other. “This. A lot of this. We’re communicating properly. We’re sharing physical affection. My ideal relationship is the one we’ve already built plus this.”

 

“So you want the hand holding and pillow talk?”

 

“I do, actually. I understand keeping a professional appearance when we’re working, but at the end of the day, after the hunt...I want us to comfort one another.”

 

Dean sighed. He liked the idea of sharing his bed with someone. “You know some people are gonna be a little pissy about two dudes holding hands and splitting milkshakes, right?”

 

“I’m aware. It is not of import. I care very deeply for you. I love you. I should not be denied the opportunity to openly express that. Nor should you.”

 

“You’re right, Cas. Just two devastatingly handsome guys making everybody jealous.” Dean pecked his lips. The whole past hour of his life felt surreal, like a Djinn dream. “This is real, right? I’m not passed out in a basement feeding a Djinn?”

 

Castiel stroked his cheek with the back of his hand. “It’s real, Dean. You always second guess when something good happens to you. I don’t want you to ‘freak out’ when you find yourself in bed with me in the morning.”

 

“If I was gonna freak out it would have been right about the time I was getting turned on by a hard dick.”

 

“You seem to enjoy the sight of them in pornography. I’ve never seen a flaccid penis on your…”

 

“Okay. Okay. I get it. I’m like a 4 on the Kinsey scale. Hot guys turn me on. You’re the only one I’ve ever had feelings for. Guys hit on me and I get all goofy. Like, how do they know? I never pictured myself sleeping with any of them.”

 

“Did you picture me?”

 

Dean blushed. “Yeah, I did. It was just a fantasy, alright?”

 

“Tell me.”

 

“Jeez, Cas. That’s a little embarrassing.”

 

“As your partner I should know how best to please you.”

 

Dean grumbled and flopped onto his back. He wasn’t going to look Cas in the eye for that. “Like stuff we did. Making out. Jerking each other off in the shower. Blow jobs. Having...having sex with you.”

 

“Penetrating me or being penetrated by me?”

 

He had to be so  _ clinical _ about it. “Sometimes one way. Sometimes the other. What, are you putting this down in a day planner?”

 

Cas put a hand on his chest. “Calm down, Dean. You said there are many ways for us to be intimate. I simply wanted to know what you were interested in trying together. Should we not be in agreement about our lovemaking?”

 

“I’m not used to talking about it. I just go with the flow. Usually I take direction from the woman I’m with and everybody’s happy. It’s different with a guy.”

 

Cas quietly processed. “Then we’ll be more vocal about our sexual needs. If I entend to perform fellatio on you I will announce it first.”

 

“You don’t need to...if we’re all hot and heavy and you wanna...just go down on me. If I wanna then I’ll go down on you.”

 

“That seems reasonable.”

 

“All I’m saying is that we don’t have to have a serious conversation to have sexy fun times. Okay? It’s supposed to be something that makes us feel good. When it happens, it happens. The only important part is that we only do it with each other.”

 

“I would never be unfaithful, Dean.”

 

“Good. ‘Cause I’m in this. I might still have to flirt a little for the job but it’s just that.  _ You're  _ the only one holding a ticket to this ride.  _ Capisce _ ?”

 

“Yes, Dean. I  _ capisce _ .” Cas frowned. “I wasn’t comfortable with the waiter flirting with me.”

 

“Babe, you are drop dead gorgeous. People are gonna flirt with you. You don’t have to flirt back or nothin’. If I’m there, take my hand or put an arm around me. Show them you’re off the market without being rude. Sorry I was a little rough sounding at the bar. It’s the jealousy thing. You’re  _ my  _ Cas.”

 

“And you’re  _ my _ Dean.” Castiel assured him. He let Dean stay on his back but lifted his arm so Cas could place his head on Dean’s shoulder. “Let’s watch something for a bit. I’d like to stay just like this.”

 

“You got it, Cas.” Dean cupped his face and kissed him sweetly. “In case I fall asleep before I can kiss you goodnight.”

 

***

 

Sam knocked on the motel room door the next morning. The last thing he wanted to see was his brother and his best friend bare ass naked. He was startled by the lock turning and the door opening so quickly. Castiel answered it, wearing Dean’s clothes.

 

“Good morning, Sam. Dean is in the shower. I made coffee.”

 

“So...how’d the date go?” Sam braced himself for too much information. He regretted asking as soon as he heard himself say it.

 

“Lovely. We’ve not communicated so openly in quite some time. I believe our relationship is off to a wonderful start.”

 

Sam breathed a small sigh of relief. Maybe Dean hadn’t debauched an angel of the lord. “Relationship, huh? After one date?”

 

“Neither of us have a problem with this. We expressed our intent of fidelity and established what level of affection is appropriate in public.”

 

“That’s a very mature way to handle things. Just so you know, I’m happy for you. And I don’t mind you being open with your... _ affection _ around me. Anything past second base...best to keep that stuff private. I’d do the same around you guys if I was dating.”

 

Castiel stepped forward to embrace Sam. “Thank you.”

 

“You’re welcome, man.” Sam patted his back. Dean came out of the bathroom.

 

“You trying to steal my man, Sammy?” Dean grinned at him. He looked...radiant. Sam thought it was a good look for him.

 

“I’m happy to see you both, well...happy. You ready to grab some breakfast?”

 

“Let’s roll.” Dean put on his shoes and threw an arm around Cas.

 

***

 

Cas looked over the menu, looking for something he could pick at and Dean would finish for him. He’d just decided when the server came with a pot of coffee and to take their orders. Sam got his usual egg white and veggie omelet with turkey sausage and fruit. Cas got a sunrise special with bacon.

 

“And for you, handsome?” she aimed at Dean. This is where he would usually wink and flirt a little.

 

Cas moved his hand from the table to Dean’s thigh and looked at his mate adoringly. “He is, isn’t he?” Dean blushed. 

 

“I’ll have what hubby’s having.” Dean smiled. The waitresses eyebrows raised with the realization.

 

“I’ll get that right in for you guys.”

 

Dean put his hand over Cas’. “Smooth, babe.”

 

“I politely made my point, as we discussed. She will  _ not _ be giving you a phone number.”

 

Sam stifled his laughter. “You guys...oh, shit. At least he didn’t smite her, Dean. I don’t know which one of you is gonna be worse with the jealousy. Chill out. You’re it for each other. I guarantee if a number shows up in front of either of you, you’ll crumble it up and leave it on the table.”

 

The new couple exchanged a look then scoffed at Sam in sync. They both made the effort to smile when their meals were brought to them. Dean left her a decent ‘no hard feelings’ tip. Sam went for the back of the car when they left but Cas waved it off. Dean slipped his left hand back between the door and seat for Cas to hold.


End file.
